With Hydrocarbon Or Halogenated Hydrocarbon Reactant Patents (Class 528/247)
  • Patent number: 10858466
    Abstract: A curable composition capable of being cured at a low temperature of from room temperature to 150° C. is provided. The curable composition comprises a fluorinated polymer containing at least three functional groups represented by the following formula (F) and at least one curing agent selected from the group consisting of an isocyanate-type curing agent, a blocked isocyanate-type curing agent and an amino resin-type curing agent: —Rf1COZ1??(F) (in the formula (1), Rf1 is a fluoroalkylene group, or a fluoroalkylene group with at least two carbon atoms having an etheric oxygen atom between carbon-carbon atoms, Z1 is NR1NR2H or NR3OR4, and R1, R2, R3 and R4 are each independently a hydrogen atom or an alkyl group.
    Type: Grant
    Filed: June 25, 2019
    Date of Patent: December 8, 2020
    Assignee: AGC Inc.
    Inventors: Masahiro Ohkura, Norihide Sugiyama, Takeshi Eriguchi
  • Patent number: 10340148
    Abstract: A polymer, an organic layer composition, and a method of forming patterns, the polymer including a structural unit represented by Chemical Formula 1:
    Type: Grant
    Filed: September 14, 2016
    Date of Patent: July 2, 2019
    Assignee: SAMSUNG SDI CO., LTD.
    Inventors: Hyo Young Kwon, Ran Namgung, Dominea Rathwell, Hyeonil Jung
  • Patent number: 9587073
    Abstract: Polyhexahydrotriazine (PHT) and polyhemiaminal (PHA) materials chemically modified to include thermoplastic polymer bridging groups, and methods of making such materials, are disclosed. The materials are formed by a process that includes heating a mixture comprising i) a solvent, ii) paraformaldehyde, iii) a diamine monomer comprising two primary aromatic amine groups, and iv) a polymer diamine at a temperature of about 20° C. to less than 150° C. This heating step forms a stable PHA in solution, which can be isolated. The PHA includes covalently bonded thermoplastic polymer groups. The PHA is then heated at a temperature of 150° C. to about 280° C., thereby converting the PHA material to a PHT material that includes covalently bonded thermoplastic polymer groups.
    Type: Grant
    Filed: July 24, 2014
    Date of Patent: March 7, 2017
    Assignee: INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: Dylan J. Boday, Jeannette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
  • Patent number: 9522977
    Abstract: Polyhexahydrotriazine (PHT) and polyhemiaminal (PHA) materials chemically modified to include thermoplastic polymer bridging groups, and methods of making such materials, are disclosed. The materials are formed by a process that includes heating a mixture comprising i) a solvent, ii) paraformaldehyde, iii) a diamine monomer comprising two primary aromatic amine groups, and iv) a polymer diamine at a temperature of about 20° C. to less than 150° C. This heating step forms a stable PHA in solution, which can be isolated. The PHA includes covalently bonded thermoplastic polymer groups. The PHA is then heated at a temperature of 150° C. to about 280° C., thereby converting the PHA material to a PHT material that includes covalently bonded thermoplastic polymer groups.
    Type: Grant
    Filed: December 9, 2014
    Date of Patent: December 20, 2016
    Assignee: INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: Dylan J. Boday, Jeannette M. Garcia, James L. Hedrick, Rudy J. Wojtecki
  • Publication number: 20150018499
    Abstract: Provided are a naphthalene formaldehyde resin obtained by reacting a compound (A) represented by formula (1) and formaldehyde (B) in a molar ratio, (A):(B), of 1:1 to 1:20 in the presence of an acidic catalyst, and a deacetalized naphthalene formaldehyde resin and a modified naphthalene formaldehyde resin derived therefrom.
    Type: Application
    Filed: January 31, 2013
    Publication date: January 15, 2015
    Inventors: Naoya Uchiyama, Go Higashihara, Masatoshi Echigo
  • Patent number: 8563665
    Abstract: A modified dimethylnaphthalene formaldehyde resin obtained by modifying a polyfunctional dimethylnaphthalene formaldehyde resin having a constituent unit represented by the following general formula [1] in a molecule thereof with at least one member selected from the group consisting of a phenol represented by the following general formula [2], a naphthol represented by the following general formula [3] and a naphthol represented by the following general formula [4], provided that at least any of the naphthol represented by the general formula [3] or the naphthol represented by the general formula [4] must be included This resin is excellent in heat resistance and useful for thermosetting resins.
    Type: Grant
    Filed: December 4, 2008
    Date of Patent: October 22, 2013
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Seiji Kita, Masashi Ogiwara, Mitsuharu Kitamura, Dai Oguro, Gou Higashihara
  • Publication number: 20120171611
    Abstract: The aromatic hydrocarbon resin can be used as a coating material and a resist resin for a semiconductor, and has a high carbon concentration and a low oxygen concentration. A composition for forming an underlayer film for lithography that has excellent etching resistance as an underlayer film for a multilayer resist process, an underlayer film formed with the same, and a pattern forming method using the same are disclosed. An aromatic hydrocarbon is reacted with an aromatic aldehyde in the presence of an acidic catalyst, thereby providing an aromatic hydrocarbon resin that has a high carbon concentration of from 90 to 99.9% by mass and a low oxygen concentration of from 0 to 5% by mass. A composition for forming an underlayer film for lithography contains the resin and an organic solvent, an underlayer film is formed with the same, and a pattern forming method uses the same.
    Type: Application
    Filed: March 24, 2011
    Publication date: July 5, 2012
    Inventors: Ryuji Ideno, Seiji Kita, Masashi Ogiwara, Gou Higashihara
  • Publication number: 20110117501
    Abstract: A resist underlayer polymer, a resist underlayer composition including the same, and a method of patterning using the same, the resist underlayer polymer including a repeating unit represented by at least one of Chemical Formula 1 and Chemical Formula 2:
    Type: Application
    Filed: September 21, 2010
    Publication date: May 19, 2011
    Inventors: Jee Yun SONG, Hwan-Sung Cheon, Sung-Wook Cho, Kyong-Ho Yoon, Min-Soo Kim, Seung-Bae Oh
  • Patent number: 7910664
    Abstract: Disclosed is a novel radially multi-branched polymer. The radially multi-branched polymer includes a central molecule to which side-branches are bonded in at least three positions and has an average molecular weight of 500 to 100,000, the side-branch being selected from the group consisting of a polyalkylene oxide, a polyacrylate, a polyester, a polyamide and derivatives thereof. The radially multi-branched polymer is used for manufacturing a low dielectric insulating film to provide a low dielectric insulating film having easily controllable micropores.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: March 22, 2011
    Assignee: LG Chem, Ltd.
    Inventors: Jae Ho Cheong, Gwi Gwon Kang, Min Jin Ko, Jung Won Kang, Myung Sun Moon, Byung Ro Kim, Bum Gyu Choi, Dae Ho Kang, Jeong Man Son
  • Publication number: 20100324255
    Abstract: The present invention provides a polyfunctional dimethylnaphthalene formaldehyde resin which is polyfunctional, rich in reactivity and useful as a variety of raw materials to be modified, specifically a dimethylnaphthalene formaldehyde resin obtained by allowing (1) one kind or two or more kinds of a dimethylnaphthalene having one methyl group on each of two benzene rings in a naphthalene ring thereof and selected from the group consisting of 1,5-dimethylnaphthalene, 1,6-dimethylnaphthalene, 2,6-dimethylnaphthalene, 1,7-dimethylnaphthalene, 1,8-dimethylnaphthalene and 2,7-dimethylnaphthalene; and (2) formaldehyde to react with each other in the presence of water and an acid catalyst, the polyfunctional dimethylnaphthalene formaldehyde resin having a mean value of the number of hydrogen atoms substituted by the reaction among the six hydrogen atoms directly bonded on the naphthalene ring in the dimethylnaphthalene of from 1.8 to 3.5.
    Type: Application
    Filed: November 11, 2008
    Publication date: December 23, 2010
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Seiji Kita, Masashi Ogiwara
  • Publication number: 20100048858
    Abstract: The present invention relates to a poly(p-xylylene)-based polymer having a low dielectric constant suitable for low loss dielectrics (LLD), and an insulating material, a printed circuit board and a functional element using the same. More particularly, the poly(p-xylylene)-based polymer includes at least one repeat unit expressed by the following formula (1): wherein, at least one of R1, R2, R7 and R8 is independently substituted or unsubstituted C6-C20 aryl; the rest of R1 to R8 are each and independently H, substituted or unsubstituted linear C1-C3 alkyl, or substituted or unsubstituted branched C1-C3 alkyl; and n is an integer of 400 to 900.
    Type: Application
    Filed: February 12, 2009
    Publication date: February 25, 2010
    Inventors: Jae-Choon CHO, Andreas Greiner, Do-Yeung Yoon, Jun-Rok Oh, Keun-Yong Lee, Moon-Soo Park
  • Patent number: 7297722
    Abstract: Described is a radially multi-branched polymer represented by the following formula (I): ABi (I), which includes a central molecule (A) to which side-branches (B) are bonded in at least three positions (i?3). Also described are methods for preparing a multi-branched polymer as well as a porous insulating film including a multi-branched polymer.
    Type: Grant
    Filed: October 8, 2004
    Date of Patent: November 20, 2007
    Assignee: LG Chem, Ltd.
    Inventors: Jae Ho Cheong, Gwi Gwon Kang, Min Jin Ko, Jung Won Kang, Myung Sun Moon, Byung Ro Kim, Bum Gyu Choi, Dae Ho Kang, Jeong Man Son
  • Patent number: 7049389
    Abstract: This invention relates to a process for preparing high-purity aromatic oligomers by effectively separating an organic layer containing aromatic oligomers or the reaction products of a polycyclic aromatic compound with formaldehyde from an aqueous layer containing an acid catalyst in a simplified manner, hitherto regarded difficult to accomplish, and obtaining high-purity aromatic oligomers from the organic layer containing a reduced amount of impurities. In separating the aqueous layer containing the acid catalyst and the organic layer containing the oligomers from the reaction mixture formed by the condensation of a polycyclic aromatic compound and formaldehyde, the emulsion phase is broken by adding a nonionic or cationic surfactant in an effective amount and an alkali in an amount sufficient to neutralize 1–70% of the acid in the acid catalyst, the organic and aqueous layers are separated and the aromatic oligomers are recovered from the organic layer.
    Type: Grant
    Filed: December 26, 2002
    Date of Patent: May 23, 2006
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Toshihide Senzaki, Takahiro Imamura, Kazuyoshi Horibe, Tomoaki Yoshida, Atsuhiko Katayama, Yasuo Wada, Katsuhide Noguchi
  • Patent number: 6949291
    Abstract: The invention relates to optical devices comprising a substrate and at least one semiconductive polymer supported by said substrate, wherein said semiconductive polymer is a copolymer in which one of the repeat units is a group of formula (I) or a homopolymer in which the repeat unit is a group of formula (I): wherein: A and B are the same or different and each comprises wholly or partially an aryl moiety or a heteroaryl moiety, said moiety in A being fused to the bond a-b and said moiety in B being fused to the bond c-d, and X is a linking unit, X being such that there is a torsion angle of at least 5° between the bond a-b and the bond c-d about the bond b-d. The invention also relates to semiconductive polymers, monomers for preparing same, and methods for preparing random statistical conjugated polymers.
    Type: Grant
    Filed: September 26, 2001
    Date of Patent: September 27, 2005
    Assignee: Cambridge Display Technology Limited
    Inventors: Andrew Holmes, Rainer Martin, Ian Rees, Cedric Fischmeister, Yuguang Ma, Franco Cacialli
  • Patent number: 6720091
    Abstract: A polymeric fluorescent substance or polymeric fluorescent substance solution is disclosed which can attain higher luminous efficiency as a polymer LED. The polymeric fluorescent substance has a specific content of water or poor solvent. Also disclosed is an organic electroluminescence device comprising at least one light-emitting layer that contains substantially no particle-like foreign materials having a diameter of more than 1 &mgr;m and that has few dark spots.
    Type: Grant
    Filed: March 15, 2001
    Date of Patent: April 13, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshihiro Ohnishi, Takanobu Noguchi, Yoshiaki Tsubata, Masato Ueda, Shigeru Sasaki
  • Publication number: 20040033047
    Abstract: Optical waveguides interconnect optical information processing devices, or connect such devices with other optical communication links such as glass optical fibers. Fluoropolymers consisting of alternating perfluorocyclobutane and aryl ether linkages possess suitable properties for optical waveguides and other devices due to tunability in optical properties of the copolymers. Perfluorocyclobutane (PFCB) copolymer may be employed in solutions that exhibit a high solids content. Such solutions show useful physical properties for optical waveguide devices since the solutions are capable of achieving single step film thicknesses, when applied to a substrate, of greater than about 0.6 microns, and sometimes may achieve a thickness of 10 microns or more.
    Type: Application
    Filed: August 30, 2001
    Publication date: February 19, 2004
    Applicant: Clemson University
    Inventors: Dennis W. Smith, John Ballato, Stephen Foulger, Suresh Kumar Manthati
  • Publication number: 20030181629
    Abstract: The present invention relates to a polymer for a chemically amplified resist and a resist composition using the same. The present invention provides a polymer represented by the Formula (1) and a chemically resist composition for deep ultraviolet light comprising the same. The chemically amplified resist composition comprising the polymer represented by the formula (1) of the present invention responds to mono wavelength in a micro-lithography process and can embody a micro-pattern of high resolution on a substrate.
    Type: Application
    Filed: April 16, 2003
    Publication date: September 25, 2003
    Inventors: Deog- Bae Kim, Hyeon-Jin Kim, Yong-Joon Choi, Yoon-sik Chung
  • Patent number: 6521359
    Abstract: Provided is a polymeric fluorescent substance which emits a fluorescence in a solid state, which comprises the following repeating unit in an amount of 20 mol % or more based on the total amount of all repeating units, in the formula, X1 represents a group selected from the group consisting of —CR3═CR4—, —C≡C—, —SiR5R6—, —NR7—, —CO—, —CO—O—, —O—CO—, —SO2—, a carbon-carbon single bond, —O— and —S—. The polymeric fluorescent substance has strong fluorescence, and can be suitably used as a polymer LED and a dye for laser.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: February 18, 2003
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takanobu Noguchi, Shuji Doi, Makoto Kitano, Fumi Yamaguchi
  • Patent number: 6489432
    Abstract: The present invention provides a polymer that can be used as an anti-refelctive coating (ARC) polymer, an ARC composition comprising the same, methods for producing the same, and methods for using the same. The polymer of the present invention is particularly useful in a submicrolithographic process, for example, using KrF (248 nm), ArF (193 nm), or F2 (157 nm) laser as a light source. The polymer of the present invention comprises a chromophore that is capable of absorbing light at the wavelengths used in a submicrolithographic process. Thus, the ARC of the present invention significantly reduces or prevents back reflection of light and the problem of the CD alteration caused by the diffracted and/or reflected light. The ARC of the present invention also significantly reduces or eliminates the standing wave effect and reflective notching.
    Type: Grant
    Filed: December 22, 2000
    Date of Patent: December 3, 2002
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Min-Ho Jung, Sung-Eun Hong, Jae-Chang Jung, Geun-Su Lee, Ki-Ho Baik
  • Publication number: 20010012572
    Abstract: Disclosed are a novel polymer comprising at least one partial structure represented by the following formula (I), (II) or (III), a light-emitting device material which is the polymer, and a light-emitting device using the material: 1
    Type: Application
    Filed: December 11, 2000
    Publication date: August 9, 2001
    Inventor: Katsumi Araki
  • Patent number: 6211329
    Abstract: A process for synthesis of a polymeric polyalcohol substantially and preferably built up form polyester units and composed of a monomeric or polymeric initiator molecule to which at least one dentritic branch (dendron) consisting of a number of branching generations is added. The branching generations comprise a polymericor monomeric branching chain extender having three reactive functions of which two are hydroxyl groups. The two hydroxyl groups of the ranching chain extender is acetal protected by reaction between said two hydroxyl groups and an acetal-forming carbonyl compound, preferably an aldehyde. The acetal protected branching chain extender is then employed for addition to the initiator molecule of a first branching generation followed by an optional deprotection of the hydroxyl groups by decomposition of acetals and for addition in repeated steps of further branching generations.
    Type: Grant
    Filed: February 29, 2000
    Date of Patent: April 3, 2001
    Assignee: Perstorp AB
    Inventors: Nicola Rehnberg, Bo Pettersson, Ulf Annby, Mats Malmberg
  • Patent number: 6136200
    Abstract: A composition for the detackification and clarification of acid and alkaline paint and lacquer waste waters and paint spray booth wastes, comprising:an inorganic-organic and/or organic adduct alloy polymer composition having the formula:A.multidot.B.sup.+ .multidot.D.sup.+wherein: A=[(SiO.sub.2 /Me.sup.I.sub.2 O).sub.u Me.sup.II.sub.m Me.sub.m.sup.III(OH).sbsp.p.sup.(SO.sbsp.4.sup.).sbsp.y.sup.(Aci) (2m+3n)-p-2y].sub.rwhere r=1 to 98% bw; u=0 to 10% bw; ##STR1## where: x=0 to 98% bw; Z is a divalent substituted or unsubstituted aliphatic, cycloaliphatic, heterocyclic or aromatic radicalD.sup.+ =(PQAM).sub.wwherew=2 to 98% b.w. of polyquaternized polymer (PQAM)Me.sub.m.sup.II is selected from the divalent cationic group comprising: Mg, Zn, Ca, and Fe.sup.2+m=0 to 5Me.sub.n.sup.III is a tri-or more valent metal selected from the group comprising: Fe, Al, and Al--Zn complexes;n=1 to 20Aci is selected from the monovalent anionic group comprising Cl.sup.-, Br.sup.-, I.sup.-, NO.sub.3 --, H.sub.2 PO.sub.4 --, CH.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: October 24, 2000
    Assignee: Polymer Research Corporation
    Inventor: John J. Waldmann
  • Patent number: 5874179
    Abstract: The invention relates to nitrogen-containing polymers containing structural units of formula (I), ##STR1## where the symbols and indices have the following meanings: Ar.sup.1, Ar.sup.2, Ar.sup.3 are, identically or differently, mono- and/or polynuclear and/or condensed aryl and/or heteroaryl groups which may or may not be linked via one or more bridges carbon atoms, which may or may not be substituted;X is a single bond, --O--, --S--, --SO--, --SO.sub.2, NR.sup.3, --CR.sup.4 R.sup.5 --, --CO--, --CR.sup.6 .dbd.CR.sup.7, CR.sup.8 R.sup.9 --CR.sup.10 R.sup.11 or SiR.sup.12 R.sup.13 ;R.sup.1 -R.sup.13 are, identically or differently, H, a hydrocarbon radical having from 1 to 22 carbon atoms or Ar.sup.4, where Ar.sup.4, identical with or different from Ar.sup.1, has the same meanings as Ar.sup.1 ;n=1, 2 or 3.
    Type: Grant
    Filed: March 28, 1997
    Date of Patent: February 23, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Willi Kreuder, Hans-Heinrich Horhold, Henning Rost
  • Patent number: 5849858
    Abstract: Furfuryl alcohol/formaldehyde resins exhibiting high water compatibility and low amounts of volatile organic compounds such as furfuryl alcohol.
    Type: Grant
    Filed: April 2, 1998
    Date of Patent: December 15, 1998
    Assignee: QO Chemicals, Inc.
    Inventors: George S. Everett, George R. MacLennan, Michael C. Chen
  • Patent number: 5763560
    Abstract: A method of producing styrene derivatives expressed the general formula (2) by reacting a benzaldehyde derivative expressed by the general formula (1) with dibromomethane under the existence of zinc metal as well as an active chloride for producing various types of oxystyrene which are polymerized monomers as a photoresist material used in a high density integrated circuit process from easily available materials which also can easily be handled: ##STR1## (wherein R indicates a an alkyl group, alkoxyalkyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a 5 or 6-atom heterocylclic groups, or an alkylsilyl group); ##STR2## (wherein R indicates any of the same substituents as those described above.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: June 9, 1998
    Assignees: Honshu Chemical Industry Co., Ltd., Osaka Municipal Government
    Inventors: Kenzo Tsujimoto, Yoshiharu Ayabe, Fujihisa Matsunaga, Ikuzo Nishiguchi, Yoshio Ishino
  • Patent number: 5668224
    Abstract: Poly(alkylene dicarboxylate) polymers and copolymers having tetraalkyl- or trialkylammonium ion end groups and methods of synthesis, thereof. The methylene-containing copolymers, in general, adhere to glass and metals, including aluminum, iron, and copper. Poly(methylene-co-ethylene terephthalate) is a clear film useful in the protection of metals or glass from corrosion or scratching. Glass may be bound to glass or to metal using the polymers of the present invention or metal to metal seals may be made.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: September 16, 1997
    Assignee: Baylor University
    Inventors: A. G. Pinkus, Rajan Hariharan
  • Patent number: 5648435
    Abstract: A process of preparing multicyanate esters by: a) reacting an adduct of a tertiary amine and a phenol-formaldehyde oligomer or derivative thereof with cyanogen halide in a solvent reaction medium under conditions to form a reaction product stream containing at least one of the following compounds selected from the group consisting of tertiary amine-hydrohalide salt, solvent, and impurities, and, based upon the total weight of the reaction product stream excluding the weight of said tertiary amine-hydrohalide salt, from about 10 percent to about 40 percent of a multicyanate ester; b) recycling a portion of said reaction product stream into the mixture of step a; and c) separating and recovering said solvent and tertiary amine from said reaction product stream. The multicyanate ester products produced are useful as bonding agents in friction materials, molding materials, coatings, and adhesives.
    Type: Grant
    Filed: November 17, 1995
    Date of Patent: July 15, 1997
    Assignee: AlliedSignal Inc.
    Inventors: David W. H. Roth, Jr., Sajal Das
  • Patent number: 5644018
    Abstract: Mesophase pitch that has a softening point of no more than 250.degree. C., a pyridine-insolubles content of no more than 50% and a n-heptane solubles content of 3-10%, with the n-heptane solubles experiencing a weight loss of no more than 15% at 450.degree. C. as measured by thermogravimetry is produced by polymerizing a condensed polycyclic aromatic hydrocarbon or a substance containing it in the presence of HF and BF.sub.3. This mesophase pitch is suppressed satisfactorily in its tendency to smoke during spinning and, additionally, it has a low enough softening point to exhibit outstanding spinnability. Hence, the pitch allows for high-volume spinning to be performed continuously for a prolonged time without causing extensive fouling of the surface of spinning nozzles.
    Type: Grant
    Filed: June 30, 1995
    Date of Patent: July 1, 1997
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takashi Kojima, Yasuhiro Hirai, Takafumi Yoshimura
  • Patent number: 5563235
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: October 8, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5483013
    Abstract: The present invention is directed to a process of preparing multicyanate esters by: a) reacting an adduct of a tertiary amine and a phenol-formaldehyde oligomer or derivative thereof with cyanogen halide in a solvent reaction medium under conditions to form a reaction product stream containing at least one of the following compounds selected from the group consisting of tertiary amine-hydrohalide salt, solvent, and impurities, and, based upon the total weight of the reaction product stream excluding the weight of said tertiary amine-hydrohalide salt, from about 10 percent to about 40 percent of a multicyanate ester; b) recycling a portion of said reaction product stream into the mixture of step a; and c) separating and recovering said solvent and tertiary amine from said reaction product stream.The multicyanate ester products produced according to the present invention are useful as bonding agents in friction materials, molding materials, coatings, and adhesives.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: January 9, 1996
    Assignee: AlliedSignal Inc.
    Inventors: David W. H. Roth, Jr., Sajal Das
  • Patent number: 5371171
    Abstract: A poly(methylene oxalate) polymer [poly(oxy(1,2-dioxo-1,2-ethanediyl)oxymethylene)], a bis(tetrabutylammonium) oxalate salt, methods of synthesis thereof and methods of use. Poly(methylene oxalate) is insoluble in all common organic solvents, does not melt and is resistant to fire. Applications are as a light-weight material for use at high temperatures, e.g. as a structural material in aircraft and space vehicles, as a binder for brake systems, and as an insulator for microelectronic components.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: December 6, 1994
    Assignee: Baylor University
    Inventors: A. G. Pinkus, Rajan Hariharan
  • Patent number: 5294352
    Abstract: A composition for the detackification and clarification of acid and alkaline paint and lacquer waste waters and paint spray booth wastes, comprising:an inorganic-organic and/or organic adduct alloy polymer composition having the formula:A.multidot.B.sup.+ .multidot.D.sup.+wherein:A=[(SiO.sub.2 /Me.sup.I.sub.2 O).sub.u Me.sup.II.sub.m Me.sub.m.sup.III(OH) p.sup.(SO 4.sup.) y.sup.(Aci) (2m+3n)-p-2y].sub.4wherer=1 to 98% bw;u=0 to 10% bw; ##STR1## where: x=0 to 98% bw; Z is a divalent substituted or unsubstituted aliphatic, cycloaliphatic, heterocyclic or aromatic radicalD.sup.+ (PQAM).sub.wwherew=2 to 98% b.w. of polyquaternized polymer (PQAM)Me.sub.m.sup.II is selected from the divalent cationic group comprising: Mg, Zn, Ca, and Fe.sup.2+m=0 to 5Me.sub.n.sup.III is a tri-or more valent metal selected from the group comprising: Fe, Al, and Al-Zn complexes;n=1 to 20Aci is selected from the monovalent anionic group comprising Cl.sup.-, Br.sup.-, I.sup.-, NO.sub.3 --, H.sub.2 PO.sub.4 --, CH.sub.3 COO.sup.-, OH.
    Type: Grant
    Filed: April 15, 1993
    Date of Patent: March 15, 1994
    Inventor: John J. Waldmann
  • Patent number: 5254665
    Abstract: Ammeline-melamine-formaldehyde resins (AMFR) containing from 5-100% ammeline were synthesized by the polymerization of the sodium salt of ammeline, which must be made in advance, melamine, and formaldehyde in basic medium (pH=9.2-10.0). In this copolymerization, it is possible to make uniform random AMFR resins with any mole ratio of ammeline salt to melamine. Preferably the AMFR resin will contain from 5-10% ammeline. As an "ionomer" or a "polyelectrolyte," both the solid and solution properties of these resins (such as melting temperature, solubility, solution stability, etc.) depended directly on the mole ratio of ammeline to melamine and formaldehyde, and/or on the pH value of the medium in which the AMFR resin was present. The pH value controlled the ammeline rings/ammeline's salt groups and also the ratio of unprotonated to protonated amino groups on both the melamine and ammeline rings.
    Type: Grant
    Filed: August 24, 1992
    Date of Patent: October 19, 1993
    Assignee: Melamine Chemicals, Inc.
    Inventors: George M. Crews, Shen Ji, Charles U. Pittman, Jr., Ruicheng Ran
  • Patent number: 5158611
    Abstract: A process for producing a resin is disclosed, comprising reacting (a) a polyalkylenepolyamine, (b) an alicyclic dibasic carboxylic acid and/or a reaction product having a free carboxyl group that is obtained by reacting an alicyclic dibasic carboxylic acid with a glycol, (c) a urea, and (d) an aldehyde and/or an alkylating agent. The resulting resin is useful as a wet strength agent to provide a paper coating composition having improved printability and printing effects.
    Type: Grant
    Filed: August 22, 1991
    Date of Patent: October 27, 1992
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Shigeru Ura, Haruo Tanaka, Hisao Takagishi, Yoshiya Fukuyama, deceased, Hiroko Fukuyama, heir, Takuya Fukuyama, heir, Yuko Fukuyama, heir
  • Patent number: 5081219
    Abstract: An open chain poly Reissert can be formed by the initial reaction of an aromatic dialdehyde (e.g., terephthaldicaboxaldehyde) and ammonia or a primary amine (e.g., methylamine) to form a reaction product which is then reacted with an aliphatic acid chloride (e.g., adipoyl chloride).
    Type: Grant
    Filed: October 3, 1990
    Date of Patent: January 14, 1992
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Harry W. Gibson, H. R. Jois Yajnanarayana
  • Patent number: 5064934
    Abstract: Thermosetting Schiff base resins, their preparation and their applications re described.These thermosetting Schiff base resins can be defined as responding to the general formula: ##STR1## Radicals Ar.sub.1, Ar.sub.2 and Ar.sub.3 are chosen so that the softening temperature of the resins is less than about 150.degree. C.The resins can be prepared by direct condensation of an ethynyl benzaldehyde or acetophenone on a telechelic diamine oligomer obtained by reaction of a diamine containing flexibilizing groups on a derivative of benzhydrol tetracarboxylic acid. These Schiff base resins can be used by bulk thermal polymerization particularly to prepare adhesives or composite matrices.
    Type: Grant
    Filed: April 2, 1990
    Date of Patent: November 12, 1991
    Assignee: Centre d'Etude des Materiaux Organiques pour Technologies Avancees
    Inventors: Regis Mercier, Thierry Pascal, Bernard Sillion
  • Patent number: 5034501
    Abstract: A process for producing a resin is disclosed, comprising reacting (a) a polyalkylenepolyamine, (b) an alicyclic dibasic carboxylic acid and/or a reaction product having a free carboxyl group that is obtained by reacting an alicyclic dibasic carboxylic acid with a glycol, (c) a urea, and (d) an aldehyde and/or an alkylating agent. The resulting resin is useful as a wet strength agent to provide a paper coating composition having improved printability and printing effects.
    Type: Grant
    Filed: September 18, 1990
    Date of Patent: July 23, 1991
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Shigeru Ura, Haruo Tanaka, Hisao Takagishi, Yoshiya Fukuyama, deceased
  • Patent number: 5006633
    Abstract: An electroactive polymer is obtained by doping a copolymer represented by the following general formula (I): ##STR1## wherein R.sup.1 is hydrogen or a hydrocarbon residue having 1 to 20 carbon atoms; R.sup.2 is hydrogen, a hydrocarbon residue having 1 to 20 carbon atoms, furyl, pyridyl, nitrophenyl, chlorophenyl, or methoxyphenyl; l is an integer not smaller than 2; m is an integer not smaller than 1; and n is an integer not smaller than 2.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: April 9, 1991
    Assignee: Nippon Oil Company, Limited
    Inventors: Yutaka Shikatani, Naoki Kataoka, Yoshiyuki Shimo, Nobuyuki Kuroda, Kazuo Matsuura
  • Patent number: 5004798
    Abstract: Cationic copolymerization of trioxane and trimethylolpropane (TMP) formal or its ester derivatives yields acetal copolymers having pendant functional groups. The TMP formal or ester derivatives of TMP formal may therefore include functional groups selected from hydroxyl or ester moieties which are protected and thus survive the copolymerization with trioxane. These groups may then be present as functional reactive sites for the subsequent synthesis of block copolymers and/or to chemically bind modifiers to the acetal copolymer backbone, for example.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: April 2, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Jerry A. Broussard, Andrew B. Auerbach, Nan L. Yang, James L. Paul, Yong C. Zheng, Chong L. Zhang
  • Patent number: 4983708
    Abstract: Cationic copolymerization of trioxane with glycidyl ester derivatives, preferably glycidyl acrylate derivatives, produces thermally stable, usually cross-linked, acetal copolymer. The resulting acetal copolymer will exhibit side chain ester functionality, and particularly side chain vinyl functionality when glycidyl acrylate derivatives are employed, so as to permit its futher reaction with other chemical moieties to achieve an acetal copolymer of modified chemical and/or physical properties.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: January 8, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Nan L. Yang, Andrew Auerbach, Rose. Pesce, Jerry A. Broussard, James L. Paul
  • Patent number: 4975519
    Abstract: Cationic polymerization of trioxane and a mixture of ester derivatives of .alpha.,.alpha.- and .alpha.,.beta.-isomers of glycerol formal yields acetal terpolymers having pendant functional groups (i.e., ester groups, or hydroxyl groups obtained by hydrolyzing ester groups, pendent from the polymer's backbone). The glycerol formal monomers employed in this invention may include functional groups selected from ester moieties which are protected from, and thus survive, the polymerization process with trioxane. These groups may then be present as functional reactive sites for the subsequent synthesis of block polymers and/or to chemically bind modifiers to the acetal terpolymer backbone, for example.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: December 4, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Nan L. Yang, Andrew Auerbach, Rose Pesce, Jerry A. Broussard, James L. Paul
  • Patent number: 4975518
    Abstract: Cationic copolymerization of trioxane and 1,2,6-hexanetriol formal (HTF) or its ester derivatives yields acetal copolymers having pendant functional groups. The HTF formal or ester derivatives of HTF may therefore include functional groups selected from hydroxyl or ester moieties which are protected, and thus survive, the copolymerization with trioxane. These groups may then be present as functional reactive sites for the subsequent synthesis of block copolymers and/or to chemically bind modifiers to the acetal copolymer backbone, for example.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: December 4, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Jerry A. Broussard, Andrew B. Auerbach, James L. Paul
  • Patent number: 4952667
    Abstract: Provided is a copolymer having a repeating unit represented by the general formula ##STR1## wherein Ar represents ##STR2## wherein R.sup.1 represents hydrogen or a hydrocarbon group having 1 to 20 carbon atoms, R.sup.2 represents hydrogen, a hydrocarbon group having 1 to 20 carbon atoms, furyl, pyridyl, chlorophenyl, nitrophenyl or methoxyphenyl, n is 1 or more and an electroactive polymer obtained by doping the above copolymer.
    Type: Grant
    Filed: June 8, 1988
    Date of Patent: August 28, 1990
    Assignee: Nippon Oil Company, Limited
    Inventors: Yutaka Shikatani, Hobuyuki Kuroda, Naoki Kataoka, Yoshiyuki Shimo, Kazuo Matsuura, Etsuo Kawamata, Hiroshi Kobayashi
  • Patent number: 4929713
    Abstract: An open chain poly Reissert can be formed by the initial reaction of an aromatic dialdehyde (e.g., terephthaldicaboxaldehyde) and primary amine (e.g., methylamine) to form a reaction product which is then reacted with an aliphatic acid chloride (e.g., adipoyl chloride).
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: May 29, 1990
    Assignee: Virginia Polytechnic Institute and State University
    Inventors: Harry W. Gibson, Yajnanarayana H. R. Jois
  • Patent number: 4904516
    Abstract: A process for preparing a water soluble phenol-formaldehyde resole resin having improved storage stability employs a calcium compound to catalyze the condensation reaction which occurs under basic conditions. Sulfamic acid is used to neutralize the resole solution, yielding a soluble calcium salt which will not settle out of the solution or clog transfer lines or spray nozzles as may a calcium salt precipitated during the neutralization. Glass fiber insulation produced using a binder prepared with the aqueous resole solution shows enhanced thickness recovery and lower odor potential.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: February 27, 1990
    Inventor: Albert W. Creamer
  • Patent number: 4891126
    Abstract: Pitch that is obtained from a condensed polycyclic aromatic hydrocarbon and the content of an optically anisotropic phase in which is substantially 100% is disclosed. This mesophase pitch has a H/C atomic ratio of 0.5-1.0, contains naphthenic carbon in an amount of at least 7% of the total carbon, and has a softening point of 180.degree.-400.degree. C. Fibers melt-spun from this mesophase pitch can be converted to carbon or graphite fibers having high strength and modulus of elasticity by a heat treatment which consists of heating to a temperature of 250.degree.-300.degree. C. in an air atmosphere, then heating to 1,000.degree. C. or higher in an inert gas atmosphere. Such mesophase pitch is produced by polymerizing a condensed polycyclic aromatic hydrocarbon for 5-300 minutes at a temperature of 180.degree.-400.degree. C. and at a pressure of 5-100 atmospheres in the presence of 0.1-20 moles of HF and 0.05-1 mole of BF.sub.3 per mole of the condensed polycyclic aromatic hydrocarbon.
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: January 2, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Isao Mochida, Yukio Sakai, Hiroyuki Otsuka
  • Patent number: 4877859
    Abstract: The present invention provides a fluroine-containing novolak resin or its derivative having a repeating unit of the formula ##STR1## wherein R.sup.1 is hydrogen atom, OH or ##STR2## R.sup.2 is hydrogen atom or alkyl group having 1 to 4 carbon atoms, X is fluorine-containing monovalent organic group having 2 to 20 carbon atoms.The present invention also provides a perfluoroalkenyloxphenol or its derivative of the formula ##STR3## wherein R.sup.10 is OH or ##STR4## R.sup.11 is H, OH, alkyl group having 1 to 4 carbon atoms or ##STR5## Y is perfluoroalkenyl group having 6 to 14 carbon atoms.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: October 31, 1989
    Assignee: Daikin Industries, Ltd.
    Inventors: Sinji Tamaru, Motonobu Kubo, Masato Kashiwagi
  • Patent number: 4839460
    Abstract: A process for the preparation of novel polymers comprises reacting a primary polyether polyamine of the formulaA(E.sub.p NH.sub.2).sub.m,wherein A is the residue of a polyether initiator having m initiator groups, E is an ether moiety from an oxirane compound, p is 5-90 and m is 2-8; with an aqueous solution of formaldehyde or with paraformaldehyde in the absence of a diluent.
    Type: Grant
    Filed: February 25, 1988
    Date of Patent: June 13, 1989
    Assignee: The Dow Chemical Company
    Inventor: David C. Molzahn
  • Patent number: 4833230
    Abstract: A new class of polyhydroxypolyamides is disclosed. The polyhydroxypolyamides, useful as fibers, plastics, coatings and adhesives, are characterizied by the repeating structural unit--CO--(CHOH).sub.x --CO--NHCH.sub.2 --(CR.sup.1 H).sub.y --CH.sub.2 NH].sub.nwhere R.sup.1 and R.sup.2 are the same or different and are hydrogen, C.sub.1 -C.sub.50 alkyl, C.sub.2 -C.sub.50 alkenyl or C.sub.7 -C.sub.50 aralkyl; x is an integer of 1 to 6; y and z are the same or different and are 0 or an integer of 1 to about 30; and n is an integer of at least about 10.A process for making these polyhydroxypolyamides is also taught. It includes the steps of reacting an aldaric compound, said compound selected from the group consisting of a diacid, an acid-lactone, a dilactone and mixtures thereof, with an alkanol to form an esterification product and forming the polyhydroxypolyamide by polymerizing the esterification product with a primary amine in a polar solvent.
    Type: Grant
    Filed: June 21, 1988
    Date of Patent: May 23, 1989
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Donald E. Kiely, Tsu-Hsing Lin
  • Patent number: 4801372
    Abstract: A novel optically anisotropic pitch is provided which is produced by thermal modification of a polymer having a structure of an alkylbenzene and a condensed aromatic compound with two to four fused rings bonded to each other via a methylene group.In preferred embodiments, the optical anisotropy is 80% or more. As the alkylbenzene there may be used xylene, trimethylbenzene or tetramethylbenzene. As the condensed aromatic compound with two to four fused rings, there may be used naphthalene, anthracene, phenanthrene, or naphthacene. The polymer starting material may be obtained by the reaction of a xylene formalin resin, mesitylene formalin resin or alkylbenzene and a condensed aromatic compound with two to four fused rings in the presence of a protonic acid as a catalyst.
    Type: Grant
    Filed: October 2, 1986
    Date of Patent: January 31, 1989
    Assignee: Mitsubishi Oil Co., Ltd.
    Inventors: Kazuhito Tate, Hajime Yoshida, Teruhiko Sasaki